Comedy set in Manhattan starring Campbell Scott as the eponymous Roger, a smooth-talking, cynical advertising copywriter who prides himself on his ability to talk his way into women's hearts and beds. Roger's smugness gets a dent when he discovers that his boss, Joyce (Isabella Rossellini) wants to end their clandestine affair, and things get worse when his teenage nephew Nick (Jesse Eisenberg) turns up at his office unexpectedly; Nick, having heard from his family about Roger's reputation as a ladies' man, has come to seek his advice about how to lose the burden of his virginity. The two go on a wild night out through the nightlife of Manhattan, but as the evening progresses, it becomes clear that Roger is the one who still has a lot to learn.